We studied geographic as well as individual variation of songs in five Czech populations of the Tree Pipit (Motacillidae: Anthus trivialis), a passerine bird with a medium-sized syllable repertoire and complex song. We focused on repertoire composition at the level of syllables (the smallest invariant song units) and of structures that are potentially important in recognition among individuals (i.e., bi-syllables, or regular repetitions of two different syllables) and among populations (introductory phrases). We tested the hypotheses that the repertoires reflect local dialects (i.e., different male origins) and that within-site similarities of male repertoires are distance dependent. The populations studied differed significantly in all analyzed characteristics. Male origin explained ∼18% of the variation in individual syllable repertoires. However, no clear within-site geographic structure in repertoire similarity was observed, either between closest neighbors or on larger scales. We observed a tendency for increased syllable sharing among males in a small and dense isolated population, which is consistent with recent studies that suggest the existence of strong effects of habitat fragmentation on geographic patterns of song variation. High individual variation was observed in bi-syllable repertoires, but whether this facilitates individual recognition is unknown and in need of further study.